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Before they had their Beverly Hills mansions and summer homes in The Hamptons, many of the most successful names struggled just to pay the rent. See which stars split the bills...

Raven Simone and Lindsay LohanThe two teen stars were roomies back before Lohan became a tabloid sensation. In fact it’s rumored Simone still gets frustrated when reporters ask her about Lindsay’s current legal troubles and frequently reminds the media she hasn’t lived with Lilo since they were practically kids.

Ben Affleck and Matt DamonOne of the most famous A-list roommate pairings resulted in a lifetime of stardom for Ben Affleck and Matt Damon. Who knew that the two Beantown boys would pen the Oscar winning script for Good Will Hunting while living together as besties in Boston.

Kiefer Sutherland and Robert Downey Jr.Many sexy stars from the ’80s were known for partying together, but it isn’t widely known that two of the biggest scenesters actually also shared an abode. Keifer fessed up to living with Downey for three years during a 2009 television interview on Jimmy Kimmel Live.

Judd Apatow and Adam SandlerJudd Apatow and Adam Sandler are two of Hollywood’s heaviest hitters, so it’s hard to imagine them living together in a cramped Los Angeles apartment. Their time together was so memorable it was actually the inspiration for several scenes in the movie Funny People.

Danny DeVito and Michael DouglasThe duo lived together in New York after meeting during the summer theater season. Douglas jokes about Devito being a great roommate because he was seldom there, saying DeVito was too busy courting his future wife Rhea Perlman to be spending a lot of time at home.

Holly Hunter, Frances McDormand, The Coen brothers, and Sam RaimiThese five dynamic and successful Hollywood heavy hitters all shared a home in Los Angeles in 1984. We can only imagine the creative juices that were flowing within those walls.